50 Fastest Horses to Ever Win the Kentucky Derby
The Kentucky Derby is, for many horse-racing fans, the pinnacle race of the year. “The Run for the Roses” is the start of the journey toward the elusive Triple Crown — an award a horse achieves by winning the Kentucky Derby, the Preakness and the Belmont Stakes all in one year.
Steeped in tradition that goes back to the first Kentucky Derby in 1875, ladies still don colorful bonnets and hats to the race, and everyone bets on their favorites. Even if the Triple Crown does allude them, winning the Kentucky Derby is a feather in any jockey’s cap. In its 146-year history, the Derby has seen some incredible equine athletes. Here are the 50 fastest Kentucky Derby horses to ever win from 1875 to 2020.
50. Mine That Bird
Year won: 2009
* All times were sourced from Twinspires.
Bottom Line: Mine That Bird
Mine That Bird began his career strongly, being voted Canadian Champion Two-Year-Old Male Horse in 2008. That same year, the horse won the Silver Deputy Stakes, the Swynford Stakes and the Grey Stakes.
During the 2009 Kentucky Derby, Mine That Bird began the race far behind but managed to catch up and win the race. He is now been inducted into the Canadian Horse Racing Hall of Fame.
49. Count Turf
Year won: 1951
Bottom Line: Count Turf
Winning was in Count Turf's blood, as his grandsire had won the 1928 Kentucky Derby and his sire, the 1943 Triple Crown.
But despite his winning bloodline, Count Turf's only notable achievement was winning the Kentucky Derby in 1951. While by no means a small feat, his performance was moderate both before his Derby win and after.
43. Venetian Way (Tie)
Year won: 1960
Bottom Line: Venetian Way
The 43rd spot on this list happens to be a six-way tie, starting with Venetian Way. Named after a street in Miami Beach, this racehorse is known for two things: winning the 1960 Kentucky Derby and influencing the decision to make pain killers illegal in the race.
The horse suffered from soreness and was thus given Butazolidin before the Kentucky Derby, a practice that was legal at the moment. He went on to win the race. However, he performed at a much lower level in the Preakness Stakes since pain killers were not allowed this time.
Witnessing the impact of painkillers on Venetian Way and other horses, the Kentucky State Racing Commission decided to ban the practice.
43. Spectacular Bid (Tie)
Year won: 1979
Bottom Line: Spectacular Bid
Spectacular Bid lived up to his name, being one of the most successful racehorses of the late 20th century. He still holds the record for 1.25 miles on the dirt.
He won 26 of the 30 races he participated in throughout his career, including the 1979 Kentucky Derby and the Preakness Stakes. He was positioned to win the Triple Crown, but injured his foot before the Belmont Stakes. Even with the injury, he came in third.
During the last year of his career, he won all of his nine races and was named American Horse of the Year.
43. Gato del Sol (Tie)
Year won: 1982
Bottom Line: Gato del Sol
Gato del Sol's story is that of an underdog victory. Before winning the Kentucky Derby, the horse had not won any race of his three-year-old campaign. Because of this, very few could have predicted his win, which became the 10th highest payoff in the history of the race.
His handlers decided to not sign him up for the Preakness Stakes, thus giving up on the chance of winning the Triple Crown. The decision was unusual but did not prove to be a mistake, as the horse finished second at the Belmont Stakes.
43. Swale (Tie)
Year won: 1984
Bottom Line: Swale
In 1984, Swale made headlines for several reasons. He first won the Kentucky Derby, then went on to come in at a disappointing seventh place at the Preakness Stakes. To the surprise of many, he made a comeback at the Belmont Stakes, winning first place.
But the main reason Swale is remembered is far more tragic. Eight days after his Belmont Stakes victory, the winning horse inexplicably collapsed and died.
43. Sea Hero (Tie)
Year won: 1993
Bottom Line: Sea Hero
This famously temperamental racehorse was an unlikely winner of the Kentucky Derby.
His early career was somewhat lacking, with only a few wins obtained here and there. He began his three-year-old campaign by losing his first three starts.
The horse shocked many with his 1993 victory, but his lucky streak proved short, as he came in fifth in the Preakness Stakes and seventh in the Belmont Stakes. Nevertheless, he redeemed himself by winning the Travers, becoming the first Kentucky Derby winner to do so.
43. Silver Charm (Tie)
Year won: 1997
Bottom Line: Silver Charm
Silver Charm almost won the Triple Crown in 1997. Having been victorious at the Kentucky Derby and Preakness Stakes, he came in a narrow second to Touch Gold at the Belmont Stakes.
Still, his performance that year won him the Eclipse Award for Outstanding Three-Year-Old Male Horse. A year later, he won the 1998 Dubai World Cup.
36. Iron Liege (Tie)
Year won: 1957
Bottom Line: Iron Liege
Next up is a whopping seven-way tie in the 36th spot.
Iron Liege may have won the 1957 Kentucky Derby, but the victory did not bring him the fame it has for other horses. This is mainly because it is credited to a mistake of Gallant Man's jockey, Bill Shoemaker, rather than to Iron Liege's speed.
At the +1/16 mile, Shoemaker mistook the pole for the finish line, standing up in his irons and making Gallant Man loose his stride. This allowed for Iron Liege, who was coming in behind to edge Gallant Man out and win the race. Shoemaker was temporarily suspended, and Iron Liege got his name in the history books.
36. Tomy Lee (Tie)
Year won: 1959
Bottom Line: Tomy Lee
The second non-American-bred racehorse to win the Kentucky Derby, Tomy Lee had a promising early career. The horse won the first six races he ever ran.
Though Tomy Lee had the honor of winning the 1959 Kentucky Derby, he did not compete in the other two Triple Crown races. This decision was made by Frank Childs, his trainer, who wanted the horse to rest. After that, Tomy Lee's career took a downturn from which it never recovered.
36. Forward Pass (Tie)
Year won: 1968
Bottom Line: Forward Pass
Forward Pass' 1968 Kentucky Derby victory was shadowed by controversy. The horse actually came in second to Dancer's Image but won when the latter was disqualified after traces of phenylbutazone were found in his analyses.
The decision outraged the sports world, with some believing it was fair and others arguing that the use of the pain killer was common practice and allowed in other races. Forward Pass was the first horse in the history of the Kentucky Derby to win by disqualification.
The same year, Forward Pass beat Dancer's Image in the Preakness Stakes, proving his worth as a champion horse.
36. Seattle Slew (Tie)
Year won: 1977
Bottom Line: Seattle Slew
This Triple Crown winner was used to coming in first. The year prior to his historic triple win, he won the Champion Two-Year-Old. The year after, he won the Champion Older Horse.
In 1977, he brought home the victory for the Kentucky Derby, the Preakness Stakes and the Belmont Stakes. In the latter, he was so far ahead from all the other horses that his jockey, Jean Cruguet, stood up in the stirrups before he had crossed the finish line to salute a crowd that was already cheering him and Seattle Slew.
36. Sunny's Halo (Tie)
Year won: 1983
Bottom Line: Sunny's Halo
This Canadian Horse Racing Hall of Fame inductee was a fighter through and through. Much of his career was marked by repeated ankle injuries and problems, which were treated in indoor swimming pools.
Despite his health issues, the colt managed to be the first horse to win the Arkansas Derby and the Kentucky Derby in 1983. A year before, he earned the Sovereign Award for his outstanding two-year-old performance.
36. Winning Colors (Tie)
Year won: 1988
Bottom Line: Winning Colors
One of three fillies to win the Kentucky Derby, Winning Colors certainly earned her place in the National Museum of Racing and Hall of Fame.
The Thoroughbred was bred in Kentucky and won the 1988 Eclipse Award for Outstanding 3-Year-Old-Filly. Her four-year-old season was difficult, marked by surgery and health issues, but she still managed to win two of her seven races.
36. Real Quiet (Tie)
Year won: 1998
Bottom Line: Real Quiet
Real Quiet's crooked knees prompted his breeder to sell him, not expecting the thoroughbred to achieve much.
The joke was on him, since Real Quiet won both the 1998 Kentucky Derby and the Preakness Stakes. He narrowly lost the Belmont Stakes to Victory Gallop.
Real Quiet's narrow frame earned him the nickname, "The Fish."
35. Street Sense
Year won: 2007
Bottom Line: Street Sense
Before winning the 2007 Kentucky Derby, Street Sense had already experienced the taste of Victory. He had won both the 2006 Breeders' Cup Juvenile and the 2007 Tampa Bay Derby.
He was the first horse to win both the Breeders' Cup Juvenile and the Kentucky Derby.
34. Animal Kingdom
Year won: 2011
Bottom Line: Animal Kingdom
Animal Kingdom had the honor of winning the Kentucky Derby in a year where the race had a record-breaking crowd of 164,858.
The American thoroughbred horse was trained by H. Graham Motion and accompanied in his victory by John Velazquez. He also won the 2013 Dubai World Cup.
28. Dark Star (Tie)
Year won: 1953
Bottom Line: Dark Star
This list continues with a five-way tie, starting with Dark Star, who ran the 1953 Kentucky Derby in 2:02.00.
Kauai King (1966), Foolish Pleasure (1975), Genuine Risk (1980), Pleasant Colony (1981) and Unbridled (1990) would also win the Kentucky Derby in the same time years later.
28. Kauai King (Tie)
Year won: 1966
Bottom Line: Kauai King
Sired by the famed Native Dancer, Kauai King won the 1966 Kentucky Derby and the Preakness, failing to win the Triple Crown when he came in fourth at the Belmont Stakes. He led the way the entire time during the Derby but had to fight for the Preakness.
He just wasn’t up for it by the time the Belmont came around. He was the only Maryland-bred horse to ever win the Kentucky Derby.
28. Foolish Pleasure (Tie)
Year won: 1975
Bottom Line: Foolish Pleasure
Foolish Pleasure won the 1975 Kentucky Derby, but that’s not why his name is recognizable by millions.
He is best known for being the horse that was pitted against Ruffian, an undefeated filly, in the great match race that ultimately cost her her life.
28. Genuine Risk (Tie)
Year won: 1980
Bottom Line: Genuine Risk
Genuine Risk won the Kentucky Derby in 1980 and is one of only three fillies (female horses) to do so.
She is also one of only two fillies to compete in all three Triple Crown races.
28. Pleasant Colony (Tie)
Year won: 1981
Bottom Line: Pleasant Colony
The following year, Pleasant Colony won the Kentucky Derby with the same time of 2:02.00.
While he won the first two legs of the American Triple Crown — the Kentucky Derby and the Preakness Stakes — but not the Belmont Stakes.
28. Unbridled (Tie)
Year won: 1990
Bottom Line: Unbridled
When Unbridled retired in 2001, he had earned almost $4.5 million in career earnings.
Of course, one of his many victories included the 1990 Kentucky Derby.
27. I’ll Have Another
Year won: 2012
Bottom Line: I'll Have Another
I’ll Have Another won the Santa Anita Derby before heading to Kentucky for the Run for the Roses. In the 2012 Kentucky Derby, he was in post 19, a spot that no winner has ever come from.
Yet, a Triple Crown was not in his future. He was pulled from racing in the Belmont Stakes due to a leg injury and was retired from racing.
26. Big Brown
Year won: 2008
Bottom Line: Big Brown
In 2008, racing fans were hopeful for a Triple Crown winner in Big Brown. He had shown commanding promise in his first race in 2007, winning by 11.25 lengths. Though quarter cracks in his hooves kept him out of some races, when he came back in March 2008, he won that race by 12.75 lengths.
At the Kentucky Derby, he drew the No. 20 post, a place no Derby winner has ever come from. Yet, he swept the 2008 Kentucky Derby by 4.75 lengths and the Preakness by five lengths, remaining undefeated. But, after suffering an abscess and yet another quarter crack, he never came back the same. He finished ninth in the Belmont Stakes, and his career of seven wins in eight races was over.
21. Twenty Grand (Tie)
Year won: 1931
Bottom Line: Twenty Grand
The 21st fastest Kentucky Derby Winner is another five-way tie, starting with Twenty Grand, who won the 1931 Kentucky Derby with a time of 2:01.80.
He also gained fame for winning the Kentucky Jockey Club Stakes, setting a track record for the mile at Churchill Downs — the fastest ever run by a 2-year-old.
21. Swaps (Tie)
Year won: 1955
Bottom Line: Swaps
In 1955, Swaps was the horse to beat. In his 15 starts since he began his career in ’54, he had won 11, including the 1955 Kentucky Derby. Nashua came in second, a horse that would be considered his rival and would later beat him in the Washington Park Match Race.
Due to a hoof wall injury, Swaps did not compete in the Preakness or the Belmont Stakes, and both wins went to Nashua. However, Swaps would come back and win the Santa Anita Handicap in ’56, along with seven others of his 10 starts that year before retiring.
21. Chateaugay (Tie)
Year won: 1963
Bottom Line: Chateaugay
Like many before and after him, Chateaugay was denied his Triple Crown by one race. In his case, it was the Preakness. He won both the 1963 Kentucky Derby and the Belmont Stakes. But what really made the Kentucky-bred colt infamous was the fact that he probably would have never run if he had not had a ventriculectomy as a 2-year-old, a surgery that improved his breathing.
At the time, this surgery was not done often, and he was the first future classic winner to have it done. He is also the son of the aforementioned Swaps. More amazing is that father and son ran the race in the exact same time.
21. Majestic Prince (Tie)
Year won: 1969
Bottom Line: Majestic Prince
Majestic Prince was a favorite to win the Triple Crown, especially after his wins in the 1969 Kentucky Derby and the Preakness. Then, trainer John Longden declared he was pulling him from the Belmont due to a slight injury.
But under pressure from his owner, Frank McMahon, the colt was raced anyway. He had a poor performance that lost him his race, and he never returned to racing.
21. Riva Ridge (Tie)
Year won: 1972
Bottom Line: Riva Ridge
Just a year before the great Secretariat would shatter the racing scene, his stablemate Riva Ridge happened to win the 1972 Kentucky Derby. He came in third in the Preakness, ruining his chances for a Triple Crown, but came back to win the Belmont Stakes.
Riva Ridge was named Champion 2-Year-Old Colt in 1971 and Champion Older Horse in 1973. He lived to be just 16 when he passed away from a heart attack.
18. Middleground (Tie)
Year won: 1950
Bottom Line: Middleground
Middleground came from Texas, the King Ranch in fact. He is one of only two Kentucky Derby winners to hail from the state. Although the King Ranch was famed for its Quarter Horses, they also owned the other Texas-bred Kentucky Derby winner, Assault, who won the Triple Crown in 1946.
Middleground won the 1950 Kentucky Derby, with a time of 2:01.60, which would later be matched by Hill Gail and Bold Forbes. He went on to lose the Preakness to Hill Prince, who beat Middleground in five of their six races together. His racing career was cut short due to an injury, but in his short career, he was only out of the money once.
18. Hill Gail (Tie)
Year won: 1952
Bottom Line: Hill Gail
Although Hill Gail was a leading 2-year-old colt when he stepped into the starting gate at the 1952 Kentucky Derby, that race would be his last great triumph. He won by five lengths, but he injured his leg in the race and would never run the same again.
He is one of only five horses to win both the Kentucky Derby and the Derby Trial, where he set a record with a time of 1:35.60.
18. Bold Forbes (Tie)
Year won: 1976
Bottom Line: Bold Forbes
Before running for the roses, this Kentucky Derby winner was named the Champion Two-Year-Old in Puerto Rico in 1975. Then, in 1976, Bold Forbes would capture both the Kentucky Derby and the Belmont Stakes.
In between them, he came in third at the Preakness, ruining his chance at a Triple Crown. He died in 2000 at 27, making him the oldest living Kentucky Derby winner to date.
Year won: 1941
Bottom Line: Whirlaway
Whirlaway not only won the 1941 Kentucky Derby, but he went on to become a Triple Crown winner. But he wasn’t done. He then won the Travers Stakes, becoming the first and only horse to win all four races.
The day before the Kentucky Derby, his trainer cut away the horse’s left blinker, hoping it would stop the erratic behavior the colt was prone to. It may have been that, or maybe the rider change, that led to him sweeping the Triple Crown. He was originally buried in Normandy, France but was moved to Kentucky and is now buried at Calumet, his owner’s farm.
Year won: 2016
Bottom Line: Barbaro
The great Barbaro has a tragic story that many in racing know all too well. He quickly won over fans by winning all the races he ran leading up to the 2016 Kentucky Derby. He was given a five-week break before the big race, the first horse in over 50 years to have that long of a break before the Derby.
He was the second favorite to win and did so with gusto, leading by 6.5 lengths. Unfortunately, in the Preakness, he shattered his leg, which would eventually be the cause for his euthanasia.
Year won: 2016
Bottom Line: Nyquist
In 2016, Nyquist headed to the starting gate as an unbeaten colt. The 2016 Kentucky Derby would not change this, and he became the eighth undefeated Derby winner. He would go on to run as a 3-year-old, breaking his winning streak, finally. He won eight of his 11 career starts.
Before his Derby run, he won the 2015 Breeders' Cup Juvenile, becoming only the second horse in history to win both races.
12. Lucky Debonair (Tie)
Year won: 1965
Bottom Line: Lucky Debonair
Lucky Debonair is a Kentucky-grown colt that first made a splash in the racing scene when he won the Santa Anita Derby in a record-winning 1:47 flat. He still holds that record, shared with Sham (1973) and Indian Charlie (1998).
He went on to win the 1965 Kentucky Derby with a time of 2:01.20, which he shares with Affirmed and Thunder Gulch.
12. Affirmed (Tie)
Year won: 1978
Bottom Line: Affirmed
Affirmed is one of those racehorses that, decades later, anyone that even casually watches racing knows. He won the 1978 Kentucky Derby and then went on to capture the Triple Crown.
His overall career was spectacular, winning 22 of 29 races. In his first race, he led gate to wire and won by 4.5 lengths. He was named Horse of the Year in 1979.
12. Thunder Gulch (Tie)
Year won: 1995
Bottom Line: Thunder Gulch
In 1995, Thunder Gulch would win the Kentucky Derby with a time of 2:01.20. He would go on to place a disappointing third in the Preakness but come back to win the Belmont Stakes. These wins, along with the Florida Derby and the Travers Stakes, garnered him the U.S. Champion Three-Year-Old Colt award for the year.
Owned by Michael Tabor, he lived to the ripe old age of 26.
11. Funny Cide
Year won: 2003
Bottom Line: Funny Cide
Funny Cide, like War Emblem, made a valiant effort towards Triple Crown Glory. He won the 2003 Kentucky Derby with a fast 2:01.19 time and then went on to win the Preakness with a time of 1:55.61. However, he, too, was beaten in the Belmont Stakes, by Empire Maker, the second-place winner of the Kentucky Derby.
Funning Cide was bred in New York and owned by Sackatoga Stable, making him only the second horse bred in New York to win the Derby — the first was Clyde Van Dusen in 1929.
10. War Emblem
Year won: 2002
Bottom Line: War Emblem
War Emblem, a gorgeous black stallion, was a favorite in the hearts of many racing fans. Purchased by Prince Ahmed Bin Salman of Saudi Arabia just three weeks before the Kentucky Derby, he was transferred to the famous Bob Baffert’s training barn.
His Kentucky Derby performance was astonishing — he led the entire time, from gate to wire, and won by four lengths. He went on to win the Preakness but stumbled at the start of the Belmont Stakes, costing him the Triple Crown.
8. Fusaichi Pegasus (Tie)
Year won: 2000
Bottom Line: Fusaichi Pegasus
Fusaichi Pegasus was sired by Mr. Prospector, a stallion whose name appears on the lineage of 51 Kentucky Derby winners. He was purchased by Fusao Sekiguchi, a Japanese businessman, at a yearling sale for $4 million, making him the most expensive horse at the sale.
In 2000, he earned his worth by winning the three big races at Santa Anita and then the Kentucky Derby. He was the first favorite to win the Derby since 1979.
8. Grindstone (Tie)
Year won: 1996
Bottom Line: Grindstone
Owned by Overbrook Farm, Grindstone won the 1996 Kentucky Derby after running in just two other races, neither of which he won. Winning by just a nose, he never raced again.
Now retired, he was the only Derby winner to ever stand at stud in the Northwest United States. One of his offspring, Birdstone, won the Belmont Stakes in 2004.
Year won: 2020
Bottom Line: Authentic
Last year, in 2020, Authentic would become the first horse since 2003 to break the top 10 fastest Kentucky Derby winners list, with a time of 2:00.61. He is owned by Silverton Hill LLC and was named Horse of the Year in 2020 as well.
It was also the year that, for the first time, the Kentucky Derby was run in September instead of May due to COVID-19. This incredible stallion is also distantly related to the famous Ruffian.
6. Proud Clarion
Year won: 1967
Bottom Line: Proud Clarion
Proud Clarion was a Kentucky-bred and -owned stallion who won the Kentucky Derby in 1967. His owner/breeder was John Galbreath.
Proud Clarion was the longshot of the race, with 30:1 odds, with a non-stellar racing career up to that point. Although he won a few other skate races, the Derby was definitely the bright spot in his career.
Year won: 1954
Bottom Line: Decidedly
Decidedly was the son of Determine, who had won the Kentucky Derby in 1954, with the 58th fastest time of 2:03.00, .02 seconds faster than American Pharoah.
Outrunning his father, Decidedly won the Kentucky Derby in 1962 in just 2:00.40. He was bred in California by George Pope.
4. Spend A Buck
Year won: 1985
Bottom Line: Spend a Buck
Spend A Buck was owned by Hunter Farms (Dennis Diaz). In 1985, he won the Kentucky Derby in just over two minutes. Diaz made a choice that year to not run him in the Preakness or the Belmont Stakes because Garden State Park had offered a special award of $2 million to a horse that could win the Cherry Hill Mile, Garden State Skates, Kentucky Derby and Jersey Derby.
Since the Jersey Derby was held after the Kentucky Derby, Diaz did not want to enter Spend A Buck in the Preakness or the Belmont Stake, but instead saved him for the Jersey Derby.
3. Northern Dancer
Year won: 1964
Bottom Line: Northern Dancer
Northern Dancer won the 1964 Kentucky Derby in two minutes flat. But his real claim to fame was being the first Canadian-bred horse to win the Derby.
Owned by E.P. Taylor, Northern Dancer was bred in Oshawa, Ontario. He won the Preakness but placed third in the Belmont Stakes.
Year won: 2001
Bottom Line: Monarchos
Monarchos won the Kentucky Derby in 2001 in just under two minutes, making him the second horse to ever win with a time that fast, right on the heels of the famed Secretariat.
The gorgeous grey stallion only ran 10 times in his career, and only won four of those starts, but he definitely made his mark. He was owned by John C. Oxley and passed away in 2016.
Year won: 1973
Bottom Line: Secretariat
In 1973, a big red horse put on a show, the likes of which we will probably never see again. Owned by Penny Chenery, Secretariat won the Kentucky Derby at a blinding speed of 1:59.40. His record has never been broken.
That year, he went on to win the Triple Crown, with an incredible, 31 horse-length lead in the Belmont Stakes.